There’s no standard dress code for events any more, which always leaves me wondering: Is it better to overdress or underdress? At a film opening recently, two guys wearing baseball caps and chore jackets were the coolest people in the room. But the few times I’ve gone casual for an event, I’ve worried that I came off as impertinent at worst and out of place at best. Is there a right way to be underdressed? — Rachel, Brooklyn
This is like “Hamlet,” the S.N.L. version. You can just imagine a host wandering around a set crying, “to overdress or underdress, that is the question?” as they beat their breast and rend their doublet. In truth, there are two camps here.
On one side, there are those who hew to what could be called the school of Coco Chanel. The famous French designer believed it was always better to be underdressed and was fond of issuing such maxims as “Elegance is refusal” and “Before you leave the house, look in the mirror and take one thing off.”
On the other side are the heirs of Iris (Apfel), the geriatric influencer who died earlier this year. She lived her life according to the conviction that more is more: more prints, more bracelets, more fun.
Also in this camp is the designer Christian Siriano, who just made the purple pantsuit Oprah wore for her speech at the Democratic National Convention. “I truly feel that it is always better to be overdressed than underdressed,” he said when I asked. “I’m a designer who loves the glamour of it all, so for me there really isn’t a right way to be underdressed unless you are actually laying by the pool or at the beach.”
Even then, he said, the look should include “a fabulous big hat and bag.”
As with most belief systems, however, the choice between over- or underdressing is not really about which option is objectively better or worse; it’s about what is right for you. Either way, you may call attention to yourself, so consider whether you would rather do so for too much flamboyance or for a lack of formality.
And remember, ultimately what is going to make someone look right, whatever the purported dress code, is feeling confident in their skin. That’s what allows anyone to enter a room with their head up.
Between over and under, though, there is also a third way.
Call it the Balenciaga principle, as pioneered by the brand’s current designer, the mononymic Demna. This particular school of dressing involves what looks like casual clothing (jeans, T-shirts) that actually features couture-level workmanship and materials. Indeed, the last Balenciaga couture collection, in July, included what looked like ratty old concert tees but turned out to be shirts with hand-painted oils by the artist Abdelhak Benallou featuring images of members of the Balenciaga atelier as a heavy metal band.
That’s an extreme case, but many pieces of the “stealth wealth” trend could be lumped in the same category. Think of the Loro Piana cashmere baseball cap. Not to mention the sudden preponderance of haute jeans and chore coats. Every runway brand seems to have them.
It’s effectively trompe l’oeil casual, the fashion equivalent of the no-makeup makeup look, or having your cake and wearing it too. Because of the fabric and cut, luxury casual tends to look more … well, luxurious and expensive than casual casual. That means it allows wearers the cool of looking as if they had just tossed on any old thing, when almost as much work and decision-making may have gone into their garments as those of a person who appears to be overdoing it. Often the simplest pieces are the hardest to make.
Because of the fabric and cut, luxury casual is more expensive — often significantly so — which is the downside. Sometimes it costs a lot to look unfancy. Whether that’s worth the price is up to you.
Your Style Questions, Answered
Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.
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